Cesium carbonate → 6({2-[4-(Hydroxymethyl)-1,3-thiazol-2-yl]thieno[3,2-b]pyridin-7-yl}oxy)-2-methylbenzo[b]thiophene-3-carboxylic acid (cyclopropylmethyl)amide

HRID 1825224Notes

Reaction equation

HRID 1825224 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][CH:13]=[C:14]([CH2:16][OH:17])[N:15]=3)[S:10][C:3]=12.[CH:18]1([CH2:21][NH:22][C:23]([C:25]2[C:26]3[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:27]=3[S:28][C:29]=2[CH3:30])=[O:24])[CH2:20][CH2:19]1.C([O-])([O-])=O.[Cs+].[Cs+]>>[CH:18]1([CH2:21][NH:22][C:23]([C:25]2[C:26]3[CH:34]=[CH:33][C:32]([O:35][C:2]4[CH:7]=[CH:6][N:5]=[C:4]5[CH:8]=[C:9]([C:11]6[S:12][CH:13]=[C:14]([CH2:16][OH:17])[N:15]=6)[S:10][C:3]=45)=[CH:31][C:27]=3[S:28][C:29]=2[CH3:30])=[O:24])[CH2:20][CH2:19]1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207679226-Hydroxy-2-methylbenzo[b]thiophene-3-carboxylic acid (cyclopropylmethyl)amideHCID 22143517[2-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-thiazol-4-yl]-methanol

Product 1

HCID 207679216({2-[4-(Hydroxymethyl)-1,3-thiazol-2-yl]thieno[3,2-b]pyridin-7-yl}oxy)-2-methylbenzo[b]thiophene-3-carboxylic acid (cyclopropylmethyl)amideYield 37.4%

Procedure

This material was prepared by reacting [2-(7-chlorothieno[3,2-b]pyridin-2-yl)-1,3-thiazol-4-yl]methanol (85 mg, 0.30 mmole) with 6-hydroxy-2-methylbenzo[b]thiophene-3-carboxylic acid (cyclopropylmethyl)amide 130a (94 mg, 0.36 mmole) and Cs2CO3 (195 mg, 0.60 mmole) in a manner similar to that previously described for example 1 to give a yellow solid (57 mg, 25%). 1H NMR (DMSO-d6, 300 MHz) δ 8.56 (1H, d, J=5.46 Hz), 8.49 (1H, t, J=5.75 Hz), 8.17 (1H, s), 7.98 (1H, d, J=2.26 Hz), 7.84 (1H, d, J=8.67 Hz), 7.65 (1H, s), 7.36 (1H, dd, J=2.35, 8.76 Hz), 6.80 (1H, d, J=5.46 Hz), 4.60 (2H, s), 3.20 (2H, t, J=6.22 Hz), 2.62 (3H, s), 1.07 (1H, m), 0.47 (2H, m), 0.26 (2H, m).

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-214e7a15795d42dc9d7c24209be4c61e
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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